#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202594.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202594 loop_ _publ_author_name 'Fun, Hoong-Kun' 'Wang, Lei' 'Xu, Jian-Hua' 'Li, Xue-Mei' 'Zhang, Shu-Sheng' _publ_section_title ; Ethyl 1-acetyl-2'-methyl-2-oxo-4',5'-dihydro-1H-indoline-3-spiro-5'-oxazole-4'-carboxylate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1827 _journal_page_last o1829 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C16 H16 N2 O5' _chemical_formula_moiety 'C16 H16 N2 O5' _chemical_formula_sum 'C16 H16 N2 O5' _chemical_formula_weight 316.31 _chemical_name_systematic ; Ethyl 1-acetyl-2'-methyl-2-oxo-4',5'-dihydro-1H-indoline- 3-spiro-5'-oxazole-4'-carboxylate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 77.015(4) _cell_angle_beta 63.933(3) _cell_angle_gamma 88.200(4) _cell_formula_units_Z 2 _cell_length_a 9.348(2) _cell_length_b 9.614(2) _cell_length_c 9.872(2) _cell_measurement_reflns_used 3060 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.43 _cell_volume 774.3(3) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3825 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.43 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.9798 _exptl_absorpt_correction_T_min 0.9227 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.150 _refine_diff_density_min -0.157 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 2665 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0365 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.1374P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0968 _refine_ls_wR_factor_ref 0.1031 _reflns_number_gt 2290 _reflns_number_total 2665 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6245.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 774.4(3) _cod_database_code 2202594 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.30739(14) 0.57549(13) -0.14506(13) 0.0592(3) Uani d . 1 O O2 0.42104(17) 0.15219(14) -0.12144(17) 0.0745(4) Uani d . 1 O O3 0.27378(11) 0.63940(10) 0.14496(12) 0.0444(3) Uani d . 1 O O4 -0.16134(14) 0.37897(13) 0.42009(13) 0.0600(3) Uani d . 1 O O5 -0.04497(13) 0.29579(11) 0.20439(13) 0.0495(3) Uani d . 1 O N1 0.35867(13) 0.35248(13) -0.02983(14) 0.0407(3) Uani d . 1 N N2 0.00556(14) 0.64982(13) 0.25250(15) 0.0449(3) Uani d . 1 N C1 0.30131(16) 0.48861(16) -0.03393(17) 0.0403(3) Uani d . 1 C C2 0.21875(16) 0.50624(15) 0.13327(16) 0.0378(3) Uani d . 1 C C3 0.26257(15) 0.37856(15) 0.22084(16) 0.0376(3) Uani d . 1 C C4 0.23698(19) 0.34449(18) 0.37334(19) 0.0486(4) Uani d . 1 C C5 0.2924(2) 0.2187(2) 0.4264(2) 0.0580(4) Uani d . 1 C C6 0.3726(2) 0.13138(19) 0.3278(2) 0.0594(5) Uani d . 1 C C7 0.3992(2) 0.16460(17) 0.1742(2) 0.0509(4) Uani d . 1 C C8 0.34167(16) 0.28908(15) 0.12318(17) 0.0391(3) Uani d . 1 C C9 0.40784(18) 0.27915(19) -0.15106(19) 0.0506(4) Uani d . 1 C C10 0.4419(2) 0.3643(2) -0.3084(2) 0.0682(5) Uani d . 1 C H10A 0.4946 0.3077 -0.3827 0.102 Uiso calc R 1 H H10B 0.5096 0.4484 -0.3332 0.102 Uiso calc R 1 H H10C 0.3435 0.3919 -0.3113 0.102 Uiso calc R 1 H C11 0.13932(17) 0.70613(15) 0.22284(17) 0.0424(3) Uani d . 1 C C12 0.1726(2) 0.83908(18) 0.2595(2) 0.0587(5) Uani d . 1 C H12A 0.0736 0.8737 0.3226 0.088 Uiso calc R 1 H H12B 0.2292 0.9103 0.1650 0.088 Uiso calc R 1 H H12C 0.2363 0.8194 0.3148 0.088 Uiso calc R 1 H C13 0.03618(16) 0.52730(16) 0.18267(18) 0.0389(3) Uani d . 1 C C14 -0.07001(16) 0.39431(16) 0.28674(17) 0.0417(4) Uani d . 1 C C15 -0.1422(3) 0.16131(19) 0.2825(2) 0.0680(5) Uani d . 1 C H15A -0.2526 0.1787 0.3424 0.082 Uiso calc R 1 H H15B -0.1047 0.1029 0.3523 0.082 Uiso calc R 1 H C16 -0.1289(4) 0.0874(2) 0.1617(3) 0.0964(8) Uani d . 1 C H16A -0.1871 -0.0048 0.2102 0.145 Uiso calc R 1 H H16B -0.0186 0.0756 0.0994 0.145 Uiso calc R 1 H H16C -0.1725 0.1434 0.0972 0.145 Uiso calc R 1 H H13 0.0199(17) 0.5521(15) 0.0914(18) 0.039(4) Uiso d . 1 H H7 0.456(2) 0.1060(19) 0.108(2) 0.057(5) Uiso d . 1 H H4 0.185(2) 0.4065(19) 0.441(2) 0.057(5) Uiso d . 1 H H6 0.412(2) 0.045(2) 0.366(2) 0.069(5) Uiso d . 1 H H5 0.272(2) 0.191(2) 0.531(2) 0.068(5) Uiso d . 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0631(7) 0.0611(7) 0.0469(7) 0.0170(6) -0.0210(6) -0.0094(6) O2 0.0908(10) 0.0602(8) 0.0860(10) 0.0197(7) -0.0394(8) -0.0439(7) O3 0.0363(5) 0.0398(6) 0.0593(7) 0.0040(4) -0.0190(5) -0.0207(5) O4 0.0550(7) 0.0647(8) 0.0475(7) -0.0024(6) -0.0101(6) -0.0152(6) O5 0.0484(6) 0.0449(6) 0.0565(7) 0.0010(5) -0.0211(5) -0.0183(5) N1 0.0358(6) 0.0434(7) 0.0435(7) 0.0071(5) -0.0146(5) -0.0183(5) N2 0.0396(7) 0.0426(7) 0.0530(8) 0.0098(5) -0.0180(6) -0.0188(6) C1 0.0321(7) 0.0443(8) 0.0442(8) 0.0050(6) -0.0156(6) -0.0131(7) C2 0.0323(7) 0.0377(7) 0.0444(8) 0.0040(6) -0.0150(6) -0.0161(6) C3 0.0303(7) 0.0399(8) 0.0437(8) 0.0018(6) -0.0158(6) -0.0130(6) C4 0.0456(8) 0.0552(10) 0.0481(9) 0.0039(7) -0.0215(7) -0.0162(8) C5 0.0611(10) 0.0609(11) 0.0528(11) -0.0007(8) -0.0302(9) -0.0036(8) C6 0.0592(10) 0.0450(9) 0.0718(12) 0.0044(8) -0.0341(9) 0.0010(9) C7 0.0488(9) 0.0385(8) 0.0658(11) 0.0082(7) -0.0244(8) -0.0157(8) C8 0.0323(7) 0.0383(7) 0.0462(8) 0.0010(6) -0.0155(6) -0.0127(6) C9 0.0392(8) 0.0622(11) 0.0586(10) 0.0101(7) -0.0201(7) -0.0340(8) C10 0.0656(11) 0.0940(15) 0.0544(11) 0.0210(10) -0.0256(9) -0.0397(10) C11 0.0437(8) 0.0378(8) 0.0468(8) 0.0084(6) -0.0193(7) -0.0144(6) C12 0.0640(11) 0.0431(9) 0.0750(12) 0.0091(8) -0.0310(9) -0.0255(8) C13 0.0337(7) 0.0437(8) 0.0429(8) 0.0079(6) -0.0178(6) -0.0165(6) C14 0.0330(7) 0.0488(9) 0.0476(9) 0.0083(6) -0.0191(7) -0.0175(7) C15 0.0826(13) 0.0459(10) 0.0746(13) -0.0091(9) -0.0361(11) -0.0081(9) C16 0.155(2) 0.0543(12) 0.1016(18) -0.0128(13) -0.0756(18) -0.0167(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C11 O3 C2 106.69(10) ? C14 O5 C15 117.05(13) ? C1 N1 C9 125.83(13) ? C1 N1 C8 109.61(11) ? C9 N1 C8 124.12(12) ? C11 N2 C13 107.16(12) ? O1 C1 N1 127.55(14) ? O1 C1 C2 124.89(13) ? N1 C1 C2 107.48(12) ? O3 C2 C3 112.75(11) yes O3 C2 C1 111.11(11) ? C3 C2 C1 103.06(11) yes O3 C2 C13 101.65(10) ? C3 C2 C13 118.28(11) yes C1 C2 C13 110.18(11) yes C4 C3 C8 120.77(14) ? C4 C3 C2 129.68(13) ? C8 C3 C2 109.55(12) ? C3 C4 C5 118.29(16) ? C3 C4 H4 121.2(11) ? C5 C4 H4 120.5(11) ? C6 C5 C4 120.44(17) ? C6 C5 H5 119.9(12) ? C4 C5 H5 119.6(12) ? C5 C6 C7 121.78(16) ? C5 C6 H6 119.5(12) ? C7 C6 H6 118.7(12) ? C8 C7 C6 117.28(16) ? C8 C7 H7 121.9(11) ? C6 C7 H7 120.8(11) ? C7 C8 C3 121.43(14) ? C7 C8 N1 129.06(13) ? C3 C8 N1 109.40(12) ? O2 C9 N1 118.75(16) ? O2 C9 C10 123.53(15) ? N1 C9 C10 117.71(15) ? C9 C10 H10A 109.5 ? C9 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C9 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? N2 C11 O3 117.73(13) ? N2 C11 C12 127.94(14) ? O3 C11 C12 114.32(13) ? C11 C12 H12A 109.5 ? C11 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? C11 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? N2 C13 C14 114.11(12) ? N2 C13 C2 104.67(11) ? C14 C13 C2 112.86(11) yes N2 C13 H13 108.4(9) ? C14 C13 H13 107.9(9) ? C2 C13 H13 108.7(9) ? O4 C14 O5 125.38(14) ? O4 C14 C13 126.07(14) ? O5 C14 C13 108.54(12) ? O5 C15 C16 107.48(17) ? O5 C15 H15A 110.2 ? C16 C15 H15A 110.2 ? O5 C15 H15B 110.2 ? C16 C15 H15B 110.2 ? H15A C15 H15B 108.5 ? C15 C16 H16A 109.5 ? C15 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? C15 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.2004(18) ? O2 C9 1.205(2) ? O3 C11 1.3800(17) yes O3 C2 1.4411(16) yes O4 C14 1.1902(18) ? O5 C14 1.3333(17) ? O5 C15 1.450(2) ? N1 C1 1.3977(19) ? N1 C9 1.4198(19) ? N1 C8 1.435(2) ? N2 C11 1.2617(19) yes N2 C13 1.4543(18) yes C1 C2 1.532(2) yes C2 C3 1.492(2) yes C2 C13 1.5758(19) yes C3 C4 1.378(2) ? C3 C8 1.3867(19) ? C4 C5 1.386(2) ? C4 H4 0.953(18) ? C5 C6 1.379(3) ? C5 H5 0.94(2) ? C6 C7 1.385(3) ? C6 H6 0.96(2) ? C7 C8 1.379(2) ? C7 H7 0.929(18) ? C9 C10 1.481(3) ? C10 H10A 0.9600 ? C10 H10B 0.9600 ? C10 H10C 0.9600 ? C11 C12 1.481(2) ? C12 H12A 0.9600 ? C12 H12B 0.9600 ? C12 H12C 0.9600 ? C13 C14 1.506(2) ? C13 H13 0.955(16) ? C15 C16 1.478(3) ? C15 H15A 0.9700 ? C15 H15B 0.9700 ? C16 H16A 0.9600 ? C16 H16B 0.9600 ? C16 H16C 0.9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C7 H7 O2 1_555 0.93(2) 2.37(2) 2.864(2) 113(2) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C9 N1 C1 O1 -13.1(2) C8 N1 C1 O1 174.26(14) C9 N1 C1 C2 163.83(13) C8 N1 C1 C2 -8.83(14) C11 O3 C2 C3 -115.37(12) C11 O3 C2 C1 129.50(12) C11 O3 C2 C13 12.29(14) O1 C1 C2 O3 -52.54(18) N1 C1 C2 O3 130.45(12) O1 C1 C2 C3 -173.55(14) N1 C1 C2 C3 9.44(14) O1 C1 C2 C13 59.34(18) N1 C1 C2 C13 -117.67(12) O3 C2 C3 C4 52.42(19) C1 C2 C3 C4 172.31(14) C13 C2 C3 C4 -65.89(19) O3 C2 C3 C8 -126.70(12) C1 C2 C3 C8 -6.82(14) C13 C2 C3 C8 114.98(13) C8 C3 C4 C5 0.1(2) C2 C3 C4 C5 -178.98(14) C3 C4 C5 C6 0.7(2) C4 C5 C6 C7 -0.7(3) C5 C6 C7 C8 -0.2(3) C6 C7 C8 C3 1.0(2) C6 C7 C8 N1 176.63(14) C4 C3 C8 C7 -0.9(2) C2 C3 C8 C7 178.29(13) C4 C3 C8 N1 -177.36(12) C2 C3 C8 N1 1.85(15) C1 N1 C8 C7 -171.51(14) C9 N1 C8 C7 15.7(2) C1 N1 C8 C3 4.57(15) C9 N1 C8 C3 -168.24(12) C1 N1 C9 O2 -163.79(15) C8 N1 C9 O2 7.9(2) C1 N1 C9 C10 16.8(2) C8 N1 C9 C10 -171.52(13) C13 N2 C11 O3 -3.51(18) C13 N2 C11 C12 175.54(16) C2 O3 C11 N2 -6.54(18) C2 O3 C11 C12 174.28(13) C11 N2 C13 C14 134.95(13) C11 N2 C13 C2 11.10(16) O3 C2 C13 N2 -14.18(14) C3 C2 C13 N2 109.82(13) C1 C2 C13 N2 -132.07(12) O3 C2 C13 C14 -138.84(12) C3 C2 C13 C14 -14.83(17) C1 C2 C13 C14 103.28(14) C15 O5 C14 O4 2.8(2) C15 O5 C14 C13 -177.12(13) N2 C13 C14 O4 -7.6(2) C2 C13 C14 O4 111.69(16) N2 C13 C14 O5 172.28(11) C2 C13 C14 O5 -68.39(15) C14 O5 C15 C16 163.96(16)